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1. 

   

   First things first (and I honestly hope that if you click the images that are actually part of the how-to, that they get larger...haha), you want a decent reference picture. I created a new document, and set it beside my own reference.
   
   I use different colors for different levels of detail, such as this circle being pink. Also notice that the actual circle itself is drawn on a new layer, not directly onto the 'Background', so that I'm able to get rid of it later.
   
   Always, always (and I don't care how strangely shaped a person's head is), always start with a circle and a 't' as a starting guideline.

2. 

   

   In this image, I just did a basic outline of the face, not too specific, and of the shoulders and neck. This is just to get a general feel for the shape.




3. 

   

   Now you create a new layer. You already have the general shape, so take a different color (I used blue), and did a much more specific outline of the head and shoulders, also the outline of the t-shirt.

4. 

   

   Now, I start getting a good outline of the hair, glasses, eyes and nose. I'm not awesome with mouths, but that comes next. You're still using your guidelines here, for positioning of the nose, eyes, etc.




5. 

   

   Now, here's the mouth, lines in place of shadows (mostly because I was far too lazy, and I'm not very good at digital coloring), lines where wrinkles are, and an outline of the face on the shirt. I know it's not a terribly great resemblance, but I tried. It's also not the most realistic, but it's pretty decent.

6. 

   

   Here, the pink lines are gone. We're left with nothing but blue lines (on their own layer). I deleted the layer with pink lines.

7. 

   

   Now I re-outline everything, with a pale brown color, on a new layer, and add in a few details that might not've been in the image to begin with, or just more details, period.

8. 

   

   Now, I get rid of the blue lines, and fill in the 'Background' layer with a darker brown color, and sign.
   
   Tada.
   
   The way I got the image at the top, the main image, to look the way it does, is that I duplicated the background layer (after merging the brown lines and the background), and set the blend mode to Multiply, creating a more vibrant image. Merge the layers, and I'm finished.
   
   You need to have a kinda basic idea of how to work with Photoshop to follow this tutorial, or GIMP, or Paint.Net. Both of those programs use layers, as far as my knowledge goes...

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